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Organic Letters

Volumn 5, Issue 13, 2003, Pages 2347-2349

Alkylation of phosphine boranes by phase-transfer catalysis

(3) Lebel, Hélène a Morin, Sébastien a Paquet, Valérie a

a UNIVERSITÉ DE MONTRÉAL (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE; TETRABUTYLAMMONIUM;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; STOICHIOMETRY;

EID: 0141497969 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol0347139 Document Type: Article

Times cited : (59)

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- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 12414-12415
- Corey, E.J.¹ Xu, F.² Noe, M.C.³

42
- 0032539189
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 13000-13001
- Corey, E.J.¹ Bo, Y.X.² Busch-Petersen, J.³

43
- 0033547985
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (1999) Tetrahedron Lett. , vol.40 , pp. 1389-1392
- Lygo, B.¹

44
- 0033547930
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (1999) Tetrahedron Lett. , vol.40 , pp. 1385-1388
- Lygo, B.¹ Crosby, J.² Peterson, J.A.³

45
- 0032493025
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (1998) Tetrahedron Lett. , vol.39 , pp. 2997-3000
- Arai, S.¹ Hamaguchi, S.² Shioiri, T.³

46
- 0032499049
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (1998) Tetrahedron Lett. , vol.39 , pp. 2145-2148
- Arai, S.¹ Shioiri, T.²

47
- 0037127783
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (2002) Tetrahedron , vol.58 , pp. 1623-1630
- Arai, S.¹ Tsuge, H.² Oku, M.³ Miura, M.⁴ Shioiri, T.⁵

48
- 0033554053
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 6519-6520
- Ooi, T.¹ Kameda, M.² Maruoka, K.³

49
- 0034738068
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 5228-5229
- Ooi, T.¹ Takeuchi, M.² Kameda, M.³ Maruoka, K.⁴

50
- 0037164678
- For selected examples, see: (a) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353-2355. (b) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (c) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (d) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001. (e) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392. (f) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388. (g) Arai, S. ; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000. (h) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148. (i) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623-1630. (j) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520. (k) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228-5229. (l) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539-9543.
- (2002) Tetrahedron Lett. , vol.43 , pp. 9539-9543
- Shibuguchi, T.¹ Fukuta, Y.² Akachi, Y.³ Sekine, A.⁴ Ohshima, T.⁵ Shibasaki, M.⁶

51
- 0141540202
- note
- We do not think that the racemization of the product under the reaction conditions could explain the low enantiomeric excess, as the same enantioselectivities were observed when the reaction was run in the presence of 0.5 equiv of the base for less than 5 min.

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